Reaction of levoglucosenone with diazocyclopropane View Full Text


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Article Info

DATE

2009-09

AUTHORS

R. R. Rafikov, R. A. Novikov, E. V. Shulishov, L. D. Konyushkin, V. V. Semenov, Yu. V. Tomilov

ABSTRACT

Depending of the reaction conditions, reaction of levoglucosenone with diazocyclopropane generated in situ from N-cyclopropyl- N-nitrosourea under the action of bases involved either the carbonyl group to give oxaspiropentane (MeONa/MeOH, s-30 °C), or the double C=C bond to give l-pyrazoline (K2CO3, CH2Cl2, 5 °C). The latter readily reacted with diazocyclopropane at the C=O group or added as a C-nucleophile in a regio-and stereoselective Michael reaction to the C=C bond of levoglucosenone. The direction of reaction depended on the reactant ratio. The reaction of the levoglucosenone—diazomethane adduct with an excess of levoglucosenone in the presence of a base yielded similar product bearing two levoglucosenone moieties. More... »

PAGES

1927-1933

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-009-0263-4

DOI

http://dx.doi.org/10.1007/s11172-009-0263-4

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1041539094


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